Welcome to Career Clarity mini-course for Managers

This guide was designed using experience and info from 3 sources:

a. Our team’s experience managing and coaching dozens of teams across multiple companies and industries (everything from venture-backed tech startups to grocery stores, banks to call centers)

b. User research interviews with 225 employees and managers about their personal career development experience and companies approaches they’ve seen

c. Research reviews of existing management and career studies and advice from sources like Google (Project Oxygen), Gallup, and Stanford

The approach you’re about to review works with everyone from hourly employees to CEOs.

Why? Because this is a framework to have a conversation, not a path to walk.

The power here comes from taking time to think about what matters. Talking that through helps tremendously. And once you’ve had that conversation, you can better figure out where to go from here.

The manager/employee relationship is often broken.

But we don’t blame you.

Managers are expected to do a million things spanning from operations to people management. The fact that you’re reading this with (we hope) the intent of helping someone else better navigate their career means you’re already ahead of the pack.

First we’ll jump into the mindset managers can have to make this most successful, then we’ll review how you can approach the actual conversations, and finally we’ll talk about how to support your employees moving forward.

Manager Mindset

Management is the most noble of professions if it’s practiced well. No other occupation offers as many ways to help others learn and grow, take responsibility and be recognized for achievement, and contribute to the success of a team.


Clayton Christensen

One of the most difficult parts of leadership is the balance between short term and long term. This is one reason career conversations often get missed.

It rarely feels urgent to talk about the long-term personal growth of an employee. But by the time it does feel urgent, it’s too late. They are either underperforming in a role that isn’t right for them or walking out the door.

Here are 4 mindset shifts that will help you make this conversation a priority.

Mindset Shift #1: Everyone can grow in their career

It’s easy to think that career growth only equals promotion. One of the benefits of genuine conversations about career is that people realize they have growth opportunities in their current role.

Employees want to feel a sense of progress. It’s easy to give up or pass up on someone who isn’t going to be promoted for awhile. “Just put in your time” is a mindset that often gets adopted. And unfortunately that leads people unfulfilled. The #1 reason people leave companies is lack of career opportunities (LinkedIn, 2015 study).

If there isn’t a promotion, it may feel like you can’t do anything about that. But that’s not true.

Everyone can grow.

A lot of this is about perception of progress as much as it is about actual progress. 

Many years ago, airport executives at the Houston airport had an issue with complaints about the wait at baggage claim. In response, the leaders upped the number of baggage handlers in an attempt to speed things up. And it worked … at least in making things faster. The average wait time got down to 8 minutes, well within industry standards.

But the complaints didn’t stop.

When they dug further and actually spent time with customers, they observed that the issue wasn’t just the time it took bags to get from the plane to the belt. It was the wait. The walk from the gates receiving complaints only took about 1 minute. Passengers then spent the next 7 minutes waiting in airport-hell, wondering when or if their bags would ever come.

So the team made more atypical change. The gates were moved further away from baggage claim. The walk time increased 6x.

Complaints dropped to almost zero.

Part of this feeling of career progress will come from the fact that we aren’t just going to ask “Where do you want to be in 5 years”, but we’re going to talk about what matters to them and use that to craft a path forward starting today.

Mindset shift #2: You don’t need to know everything

It’s ok to not know everything, it’s ok to not have the answers … and in fact it’s best if you don’t. A good manager doesn’t need to give advice. The best managers don’t give advice. They act as coaches and advocates to help employees learn how to get their own answers.

When you don’t know an answer it’s perfectly fine to say “I’m not sure, but let’s figure it out.” Knowing that you are in their corner goes a long way, even when you aren’t sure how to answer right now.

Mindset shift #3: Priming is Powerful

Presentation impacts results.

A research group at a European university wondered how much we are impacted by the perception of how something will go. They gave wine samples to study subjects and asked them to rate the wine on a 9-point scale. As a part of the sampling process, they showed them the price of the wine (either €3, €6, or €18).

But they didn’t actually have different wines.

Each tasting used the exact same wine. Yet participants thought that the “more expensive” wines were better.

Now, you may be thinking this is simply social pressure. They didn’t really think the wines were better, they just said they were so they wouldn’t look stupid. But here’s the really interesting part:

Subjects tasted the wine while in an MRI machine.

The scans of their brains showed that when presented with wine that “should” have been better because it was more expensive, their brains actually tasted it as better.

So, what does this have to do with your upcoming career conversation? How you tee this conversation up can impact how it goes.

Here’s a 6-point continuum you can use to think about your reaction to approaching a conversation like this:

Continuum of Willingness

  • -2 Unwilling: “No, we don’t have time to do that” (or just ignoring it all together)
  • -1 Forced: “I guess”, “HR has asked that we …”, “You need to …”
  • 0 Basic: “Sure, we could do that”, “I’d like to have this conversation with you.” (willingness)
  • 1 Intermediate: “Yes, let’s totally have this conversation. I’m looking forward to it.” (excitement)
  • 2 Advanced: “Wonderful, I’m excited about this. I’ll be ready (I actually went through the manager mini-course) and am looking forward to part 1” (showing preparation)
  • 3 Sacrifice: “My job is to help you grow and contribute to the team, this is important to me so I’ve carved out time.”

Be honest with yourself about where you are on that continuum as a manager. See what you can do to move up the scale, even just one point.

Your attitude will impact how open your employee is and influence their attitude during the exercise.

Mindset shift #4: Selfishness is toxic to career conversations

The Trust Formula (from the book The Trusted Advisor) is our favorite way to think about how trust is built.

Use This Equation to Determine, Diagnose, and Repair Trust | First Round  Review

Perceived self-interest (how much someone thinks you’re only concerned with yourself) reduces trust.

As a manager this can be a hard variable to change. You have a lot of right to be self-interested.

You’re trying to grow your own career.

You’re trying to build and protect the company.

You’re trying to make sure your team doesn’t reflect badly on you (since their performance is a reflection on you).

But if an employee doesn’t feel safe to be open about ideas, career conversations won’t have the full impact they could have.

Showing selflessness to your team has ROI.

They will be more open with you in conversations, they will bring their best selves to work, and they will want to stay on your team longer.

Pitfalls to avoid

Given these mindset shifts, here are 5 pitfalls to avoid:

1. Not having the conversation.
2. Focus only on short or long term (performance reviews are not career conversations)
3. Go through the motions (instead of having real, honest conversation)
4. Don’t prepare, just do this ad-hoc
5. Give advice (we’ll discuss what to do instead of giving advice later one)

Let’s Talk: How to actually have the conversation

This core conversation can be 45-60 minutes. You could go deeper and take 3 hours, but we’ve found most managers aren’t equipped for that depth of conversation (unless you are a trained psychologist). This simple version is more than enough to get started.

The most common mistake managers make in career conversations (other than not having them) is talking too much.

Managers often think they are coaching when they are actually giving advice.

Don’t just give advice. That’s not coaching. Advice is how you would do something. Coaching is questioning to help them understand their situation and encouraging them to figure out a path forward.

Don’t use the words “You should …” There is power in them figuring out the path forward. If you push or craft the path, they may miss out on the commitment that come from the hard work of self-reflection and learning.

The magic question in these conversations is “tell me more”.

When they seem confused. “Tell me more.”
When they choose a word. “Tell me more.”
When they mention the start of a story. “Tell me more.”

If pressed, share your perspective/history as an example … and then invite them to consider how that applies to them.

Core Conversation: Past, Future, Present (conversation guide)

You can check out the core exercise guide as well as the conversation guide to understand the mechanics. 

Our advice for you as their manager: Take this time to think about them and it will benefit you and your team. 

Go as deep as they are comfortable. Be genuinely curious.

Some managers/employees like to ask questions during the card sort. Some are quieter until the end. We’ve seen either way work well.

The conversation is less about getting someone specific or accomplishing something and much more about taking time to connect and reflect. When done right, you will learn something that you didn’t know before (this is true for the individual themselves as well as for you, the manager). 

Making it stick

Now that you’ve had this amazing conversation, now what? Well, as you may experienced before, it’s easy to get excited in the moment and then go back to work as usual. The bulk of the responsibility rests with the employee (they are the owner of their own career), but here are ways you can help this carry on:

Take notes throughout the conversation. People tend to dig deeper when they know someone is taking notes. This will help you focus and you can give them the notes after the conversation as a gift to your employee.

Hold them accountable. Now, when we say “hold them accountable” maybe you’re thinking of forcing or pressuring them to stick to their career roadmap. That is not the best path forward. Accountability in this context (where an employee owns their career) needs to come from them. You are their fan. Their supporter.

Here are some phrases that can help set up healthy accountability:

  • “What can I do to support your career experiments moving forward?”
  • “How is that experiment going? What have you learned?”
  • “Has your thinking changed since we last met? Why?”

Schedule nudges. Nudges and reminders are helpful. Brains are for having ideas, not remembering them. Two tools you can use are calendars and scheduled emails.

Schedule time in a few days or weeks to reminder you to follow up or for a quick touch-base with your employee. Putting it on your calendar is a sure way to make sure this happens.

Also, many email clients now give you the ability to schedule an email in the future. This is a great way to follow up with your employee in a way that helps them (using spaced repetition, which is a proven way to more effectively learn and change). Here’s an example template you can use:

“Hey. I was thinking about the conversation we had [last week] about your career. Thanks again for being open. I’m excited about the experiments you’re going to run. Just wanted to give a friendly reminder that I’m here to support you. Let me know how I can help moving forward.


Here are the notes I took, in case that’s helpful:”

You’re ready

This is going to be great. This is a human conversation where you get to help someone else on their journey to understand what’s important, figure out what that means, and move forward.

Check out the exercise instructions and conversation guide to familiarize yourself with the process beforehand.

We’ll be adding to this guide over time and we’ll email those with manager access when there’s an update. Here’s to helping your employees bring their best selves to work through better career conversations!